


Escorting Dean

by RedheadShenanigans



Category: Supernatural
Genre: BDSM, Eventual Fluff, Gay Sex, Gratuitous Smut, M/M, One Shot, Oral Sex, Smut, So much smut, Spanking, Top Castiel, Top Castiel/Bottom Dean Winchester
Language: English
Status: Completed
Published: 2018-09-08
Updated: 2018-09-08
Packaged: 2019-07-08 18:02:42
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,456
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15935510
Author URL: https://archiveofourown.org/users/RedheadShenanigans/pseuds/RedheadShenanigans
Summary: Dean is an escort.  Castiel Novak's profile makes Dean's mouth water, and his bank balance is very promising.His kinks make Dean wanna fall to his knees and beg and they will. They message back and forth for weeks planning their adventure, tonights the night and Dean's received the message from Cas, 'I'm on my way'.





	Escorting Dean

Dean was nervous. His hands were shaking and the nausea was rolling through him in waves. Why was he freaking out? It wasn’t like he hadn’t done this before. ‘Calm down’ he ordered himself and went to splash some water on his face. The apartment he used for his work was spacious and decorated in an interesting style; five-star hotel meets sex dungeon. The rooms were all leather couches, oversized vases and high-quality floors. The bedroom, well, that was full of leather too. He walked back into the lounge and sagged into the brown leather. His suit would crease if he slouched but right now he really didn’t care. ‘It’s a three thousand dollar suit, you’ll care tomorrow’ his inner voice growled, and so he adjusted his posture accordingly.

Several deep breaths later he felt more centred and pulled out his phone. The last message was from Castiel and it read, ‘I’m on my way’. He shuddered, Jesus, just the thought of this guy in his space, in his room, had him throbbing. Dean adjusted himself and cleared his throat. Scrolling through Castiel’s profile made him crawl the walls with excitement. This was his first time working since he’d ended things with his last client. Finding Cas was like finding a box of gold at the end of the escort rainbow. In Dean’s profession, yeah the guys could be hot but they were mostly mean or cruel. Or worse narcissists and eventually for his own sanity, he’d have to step back. Cas was different. He seemed, well nice. They’d been texting and calling for a few weeks. Cas had been away on business which had been great because Dean had been able to feel the guy out.  
The profile he was browsing on his phone held all the details of the man on his way there. Cas was 28, 5’11’’ and an investment banker. The guy was loaded, like Daddy Warbucks loaded, which was a bonus. Cas had told him a lot about himself and unusually Dean had told the truth about himself which was a big no-no. Something about Cas had him letting down his walls. Maybe it had been a bad idea, he’d know soon enough. 

The knock on the door had him on his feet in a second and he walked to the door without a word. Opening it was like letting a wash of daylight into a dark room. Castiel Novak was perfect. Stunning blue eyes shone from a beautiful chiselled face. It was enough, no too much, just enough. There was a playfulness about him as he smiled. Stepping into the room he slipped off his jacket and Dean took it and hung it up. 

“Hello, Dean.” 

As they had pre-agreed, Dean fell to his knees. 

Working on this scenario for weeks meant the safe words were already in play. 

Dean moved his shaking hands to Cas’ ridiculously expensive suit pants. He slid the belt all the way out, the way he had been asked to then laid it across the arm of the couch. Undoing the buttons and the zip, the slacks fell to the floor. Cas stepped out of them and as instructed Dean folded them and placed them with the belt. The shoes were next, Dean untied the laces and Cas slipped them off. Dean moved them to the couch. Dean stood and undid Cas’ tie, so slowly it actually pained him. His cock was throbbing as it rubbed inside his tight slacks. Dean pressed his groin into Cas, grinding them together as he’d been told. The list had been detailed and extensive and like the pro he was, he had memorised it gladly. Cas’ eyes rolled into the back of his head and Dean liked that. There was no pretence, he was enjoying it. So was Dean but one of the rules was that he couldn't moan or groan until Cas gave him permission. They were a breath away from each other's lips and the temptation to close the gap was overwhelming. Cas smiled as Dean folded the tie and placed it with the rest. Moving back to Cas he slid his hands up the man’s shirt and stared with the top buttons first. Opening them was a form of torture. He had to count ten seconds between buttons. This who thing was supposed to be for Cas, it was supposed to be torture for him. He’d told Dean that he found him insanely attractive and keeping him fully clothes was part of his kink. It was also killing Dean. This guy was stunning, he would have done this for free. The buttons opened one by one and Dean had to grind his teeth together to keep from moaning. The perfect tanned skin that covered a sculpted chest was every Christmas gift Dean had asked for. This was much, much better than he’d thought. 

The shirt fell open and he stifled a gasp, the six-pack finished the view off nicely. His fingertips ached with the need touch, to explore but he wasn’t allowed. The urge to lick and kiss that perfect torso was like a kick in his gut. Flexing his hand to shake the urge he pealed the brilliant white shirt from Cas’ arms. The man did martial arts and it showed, his biceps were toned perfection. Once the shirt was folded and placed with everything else Dean had thirty seconds to stare. He was allowed time to stare he had negotiated it in once Cas had sent pics of himself from the neck down. Yep, this was heaven. Holy freaking Jesus. The only drawback to negotiating was that he’d had to give a little and he knew this was going to hurt. 

“Dean?” Cas whispered and as Dean met his eyes he wanted to beg to be dragged into the bedroom and fucked. Cas’ gaze was full of desire and longing. It wasn’t what he usually saw. 

Most of the time it was like ownership, guys wanted to possess him like a car or a watch. Cas’ eyes held a promise, something more friendly and it scared him as much as he wanted it. Dean did what he knew was required and closed the distance between them. They were within kissing distance again and Dean moved in close. One more millimetre and they’d be kissing. It was kind of the point and Cas closed it but instead of a kiss Cas used his tongue and ran it over Dean's lips. He didn’t move any other part of himself, he simply licked his sexy, wet tongue out and smoothed it over Dean’s lips. It took longer than anyone would think, at least a minute because Cas took his time. It was an effort in self-restraint on both their parts. Dean felt like he was going to die, this perfect exquisite torture was going to kill him. Cas’ tongue was wet and warm on his skin. Dean had to bite his own to keep it from doing something that they would both regret. Cas sighed peacefully as he took his tongue back. 

Dean stepped back and nearly fell, so frustrated he was dizzy. The silence in the room was deafening as Dean dropped to his knees. He looked up into Cas eyes as he wrapped the mans throbbing cock in his hand through his silk boxers. Gasping, Cas let his head fall back. Dean smiled and teased through the silk before removing them as instructed. The tease made things both better and worse. Better because this was something Dean enjoyed and worse became his skin was on fire with need. He wanted to be naked with this solid, thick cock in his ass. It was a quiet desperation that was clawing at his insides as he folded the boxers and placed them on the couch. Cas was naked, gloriously and perfectly naked. He shuddered as he slid back to his knees, the carpet cushioning his hard fall. Dean’s long fingers slid over Cas’ throbbing meat as he pulled it towards his waiting mouth. Flicking his tongue out he licked around the tip and then played the foreskin back and forth. Cas was growling his name and sweat started to form on the sexy man’s chest. Cas stood and let him run his lips up and down the near purple head that was begging to be sucked. Dean could take as much time as he wanted, it was part of the instructions, the slower the better but he had some leeway. So he devoured the part of Cas he got to touch. Staying silent was actually harder than it sounded. The instinct to moan was automatic and stopping himself caused almost physical pain. 

Dean licked and sucked Cas’ cock like it was he favourite candy. As if it was his only way to survive the night was to please the man standing before him. Cas lent back into the door for support as his legs started to give way. He was close, Dean could feel it. The sucking and the smooth caresses had him drowning in sensation. His fingers worked that tender skin and had Cas over the edge in minutes. The cum was hot and sticky in his mouth, Swallowing was something he did gladly. Dean groaned his pleasure out around Cas’ dick as it twitched with the rest of him. Then it hit him, he’d made an error. Shit. Cleaning Cas’ cock with his tongue took a few seconds. Then he stood in front of him as he straightened himself and pushed away from the door. 

“Dean. You were naughty.”

Dean didn’t reply, it wasn’t necessary. Turning, he undid his slacks and let them drop to the floor, then his boxers. Everything stayed on but his ass was bare as it faced Cas. Bending over Cas picked up the belt from Cas’ clothes and passed it to the waiting hand Cas had outstretched. Dean moved back to the couch and bent over, his hand on the arm. The snap of the belt had him shuddering and throbbing at the same time. Cas hadn’t even hit him yet and he was trembling. Cas' hand ran over his ass and he bit his lip hard to keep the groan in. Every groan got him two lashes and stopped play. Dean really wanted to get fucked tonight so he would behave where he could.  
The first strike was light and Dean knew Cas was teasing. The sting was followed with Cas playing his fingers lightly over Dean’s cheek where the leather had lefts its mark. The second came hard and fast. A whip of material on his skin and a sharp sting of pain wish had him gritting his teeth together. Cas stepped back and gean pulled his boxers and slacks back into place. 

“Bedroom?” Cas asked with a smile. Dean shivered and led the way. 

His ass stung and he was determined that was the last time that was happening before he got what he wanted. Dean was a master of control and he could do this. He was not a fucking amateur. 

The bedroom was a dungeon of sorts. The bed was huge and rugged for every piece of apparatus used in the sex industry that anyone could think up. Dean liked to play most games and if not engage he was able to inflict them on others. Cas had chosen to keep it simple. The bed, soft cuffs, ball gag and a few other toys. Though Cas had added a caveat that he could stop play whenever he wanted, just quit the scene. It was almost unheard of but Cas had made it clear that if he wanted to simply take Dean’s ass, he was doing it. That night he’d come so hard in his own hand it was a miracle he hadn’t passed out. 

“Naked. Now” Cas commended and Dean nodded. 

Stripping took a few minutes but once he was naked he crawled onto the bed. The bed was soft under his knees as he crawled onto it. Cas met him on the far side where the toys were. He handed him the ball gag and he put that on himself. When the strap slipped into place Cas simply stared at him like he wanted to know what he tasted like all over. ‘Like pure fucking need’ Dean thought to himself. The gag was firm but soft. The uncomfortable feeling stopped when his jaw adjusted. It was something he wore often and as such he was used to it. His breathing adjusted and he took the time to watch Cas watching him. The guy was practically salivating and it was amazing. Cas held the bell up, it was a small ball that when squeezed let out a sharp sound, Dean wrapped his hand around it. It was the stop signal. Soft cuffs were next up and Dean turned on his knees putting his arms behind his back. The cuffs were strapped on and then attached to the rig that hung from the ceiling. It would keep Dean still and in one place or he would pull his shoulder. The rig gave Cas something to steady himself on and something to pull if he wanted to add a little pain to Dean’s play time. 

The lube was cold over his ass and he flinched. Fingers played with his hole and he relaxed, finally he would get some release. Cas pushed firmly into his tight bud, his strong finger sliding in easily. Dean stopped the groan before it escaped. The stretch was amazing and Dean relaxed around the warmth in his ass. A second finger pushed in and Dean’s eyes fluttered closed. Holy God this was perfection. 

Cas worked his fingers in and out of Dean like a pro. Dean’s heart was trying to force its way out of his chest. His cock was so sensitive, so tense with the need to cum that one touch would send him over the edge he was sure of it. This guy, what was happening to him? 

His thoughts were interrupted. Cas withdrew his fingers and pushed a medium sized plug inside. It was three inches long and two wide. It slid in with a push from Cas’ rough hands and Dean grunted. He felt so full. The slap came sharp and fast. Cas’ skin hit his with force and Dean bit his lip to stop the moan of pleasure and pain. The snap and sting had him trembling in all the best ways. Fuck. Cas worked the plug in and out of him before the second lash came, this time it was the belt and not his hand. Slap then sting. Fuck that hurt but the pain was followed by a wash of bliss. Dean sagged letting his shoulders take all his weight.  
Cas moved around to the other side of the bed and crawled over to him. The shorter man kneeled naked and undid the gag. The kiss was hard and brutal. Dean melted into it, he bit and thrust his tongue into Cas’ as the man devoured his mouth. 

“I’m going to fuck you now Dean,” Cas said as he placed the gag on the side.  
Dean worked his jaw. He wanted to ask if something was wrong. They had planned this out to the last detail. The expectation Dean had was that there would be more teasing involved before any kissing. That had been a surprise. Dean smiled and Cas returned it, all was well. Maybe he’d explain after. Cas undid the cuffs and the rig. Dean stretched his arms out and then resumed his position on all fours. 

“On your back. I want to see you.” Cas whispered. 

Dean did as he was told and looked up as Cas crawled up his body placing feather light kisses over his skin. Cas’ cock grazed over his, both throbbing and hard as Cas’ mouth found his. 

“Touch me, Dean. Touch me like you need me.” Cas growled. 

They skipped several stages but Dean was happy to comply. Dean slid his hands all over Cas’ body, everything he could touch he did. The kissed were deep and ravenous, they had Dean panting for breath as Cas pulled back and stared into his eyes. Jesus, they were blue. 

“Sound on.” Cas breathed and Dean sighed. That meant he could say or sound any way he wanted. Thank fuck for that. He usually had more patience than this but something about this guy made him want to be close. That was not a good thing in his profession. 

“Fuck me?” Dean asked, his voice breaking as he cleared his throat. 

Cas fingers found the plug and pulled it out slowly. Dean moaned out Cas’ name and he shuddered. Feeling empty didn’t last long because Cas pushed his head into Dean waiting hole. 

It was slick enough that Dean simply enjoyed each inch as Cas worked himself inside him. Cas kissed him and Dean groaned.

“Oh Dean…fuck…” Cas sighed as he bottomed out in Dean’s ass.

“That’s so good,” Dean said as he gazed into Cas’ eyes. 

“You do you,” Cas said and Dean smiled. Taking his cock in his had was amazing. Coupled with the feeling of this perfect man in his ass, he was actually in paradise. 

Cas started to move and Deans eyes rolled back in his head. The feeling was all hard, warm pressure and stretching as Cas rolled his sexy hips over and over. Dean was over the edge in a second. All that pent-up tension had left him a bundle of raw aching nerves. One touch of his cock, one stroke of that place deep inside where all his bliss waited for release and he was done. Cas took Dean’s cock in his hand as Dean came. Their hands touched and it threw him into an orgasmic spiral. Waves of pure ecstasy rolled through him, over and over. He writhed and twitched as he felt everything. His skin pulsed with electricity and his hands dug into Cas shoulders. Like he was in the ocean and Cas was the only solid ground for miles.

Cas moved faster. Fucking him hard as Dean’s cum bathed their joined skin.

“Oh god Dean, I’m so close.”

“Cum for me.” Dean growled, “Come inside me.”

“Shit.” Cas groaned as he thrust his hot wet released inside Dean’s tight ass. 

“Holy God.”

Dean was almost crying he felt that good. Nothing had ever been that good, ever. 

Cas smiled and panted out, “Nothing has ever been that good, ever.” 

Then he rolled off Dean and onto the bed. Dean grinned as Cas echoed his thought. He was glad it wasn’t just him. They simply lay there and Dean glance at Cas and Cas glanced at him. 

“I want to look at you but it’s not something I should do is it?” Cas asked. 

Dean was startled, “Erm, it’s your money, you can look if you like.” 

Cas frowned, “What about resting your head on my chest? Would you do that?”

Dean nodded, “Sure.”

‘This is dangerous’ his inner voice called. Dean shut it down as he snuggled into Cas’ chest. Dean yawned and found himself drifting off. That woke him up. ‘Shit. What are you doing?’ he chastised himself. 

“Is there something wrong?” Cas asked. 

“No… It’s just this is too… comfortable and I think it’s crossing a line for me.” 

Cas frowned again and Dean wanted to kiss it from his face. Sirens started to blare In his mind and he shuffled back.

“You should go.” 

“Why?” Cas asked with a confused stare. 

“Because I like you… this isn’t going to work. I’m sorry.” Dean whispered as his heart tore. 

“I like you too,” Cas said as he moved closer. 

“You do?”

“Yeah. Assuming you were honest with me while we were talking?”

Dean nodded, “That was my first mistake.” 

“I want to date you, Dean… for real.” 

“Why?” Dean growled out. He’d heard this before and the guy always left eventually. Someone always wanted to save him from this life. 

“Because when I talk to you, I don't want to do anything else. Because you’re smart and funny and we like all the same old movies. Because you see me and it doesn’t scare me. Because I see you and this last few weeks have been the best of my life because you’ve been in them.” 

Dean stared and his jaw fell open. 

“I rehearsed that a little in case, you know…” 

Dean’s heart tugged and he caved as Cas stared at him with those sad blue eyes. Shit. “Okay.”

Cas grinned and Dean melted. 

Oh yeah, he was fucked and not just in a good way. 

 

-fin-

**Author's Note:**

> I was forced into writing this by Mali and her evil prompt. So I'm not sleeping, I'm posting smut. Do you hear me Mali! No sleep, smut! Anyway, thanks for reading, I love you all! (Not Mali) I'm sorry if it's not perfect, I'm tired. 
> 
> https://www.tumblr.com/blog/redheadshenanigans


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